Holbrook entered the 2004 grand final against perennial powerhouse Osborne as favourites.
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Coached by Marc Duryea, the Brookers had finished minor premiers and took the direct route into the decider.
They were searching for their maiden flag in the Hume league after joining the competition in 1999.
Despite their favourites tag, there was still plenty of pressure on the Brookers who also had to contend with their mental demons.
They had let two golden opportunities slip to win their first Hume league flag in 2001 and 2003 after suffering grand final heartache against Osborne and Lockhart respectively.
Michael Buchanan was coach of the Cats and was a premiership teammate of Duryea's at Albury.
However, Buchanan was forced to withdraw from the grand final after straining his hamstring in the preliminary final against Howlong.
The match started in disastrous fashion for the Brookers after dogged onballer Danny Whitley was given a free trip to Disneyland in the opening minutes after courageously running back with the flight of the ball.
Heavily concussed, Whitley took no further part in the match, robbing the Brookers of a midfield rotation.
The Cats were also able to apply some early scoreboard pressure.
They booted five goals to one in an opening term blitz and the Brookers trailed by 29-points early in the second-quarter.
History says Osborne rarely loses grand finals from there.
Duryea recalled firmly staring down the barrel of further grand final heartache at quarter-time of the decider.
"We lost Danny Whitley in the first minute and I regard it as the biggest hit I've seen during my time of playing footy," Duryea said.
"It wasn't dirty, he was just running back with the flight of the ball and into a spot where you shouldn't go.
"It was a massive hit and even in the rooms at half-time, they didn't want to move Danny and he was still in and out of consciousness.
"So Danny was knocked out and all of sudden early in the second-quarter we were five goals down."
With the Brookers on the ropes, most spectators expected the league heavyweight to land the knockout blow in the second term and waltz away with yet another flag.
But it was Duryea who was playing in the centre who was able to lead a courageous fightback with the Brookers booting the next five goals to snatch the lead shortly before the half-time siren.
It was a lead they would never surrender as they piled on eight goals to three in the second half to clinch their maiden Hume league flag in style.
Fittingly, it was Jack Parker who put the grand final out of Osborne's reach, kicking a goal midway through the final term.
Parker, a Brooker stalwart playing in his final match, snuck down from defence to give his side a match-winning lead of 18-points in a fairytale end to his career.
It was the only goal he kicked during his six seasons in the Hume league.
"I remember when Jack, who was a defender and hadn't probably kicked a goal in the four years that I was coach, kicked a goal midway through the last quarter," Duryea said.
"It was at that moment that I thought to myself 'I've got a good feeling about this now, if something like that is happening... I think we might be on here.'"
The Brookers will hold a 2004 reunion this weekend to reminisce about their first flag in the Hume league.
Duryea said 19 of the 21 premiership players will be in attendance on the weekend.
Three fathers who played in the flag in Marty Semmler who was skipper, Jack Parker and Nick Moore will have sons playing against Osborne in the seniors on the weekend in Lachie Semmler, Fletcher Parker and Ethan Moore.
Lachie joined the Brookers this season from Lavington thirds while Ethan played in the Brookers' reserves flag last year.
Fletcher played in the Brookers' reserves flag two years ago and in their losing senior grand final last year but is out with a leg injury for the next few weeks.
Holbrook 1.4 6.6 10.8 14.9 (93)
Osborne 5.2 6.4 8.8 9.11 (65)
Goals: HOLBROOK: J. Way 3, N. Coutts 3, T. Hickey 2, D. Hargreaves, T. Nichols, Jarrod Hillary, J. Parker, J. Hollard, J. Culph; OSBORNE: H. Gleeson 3, S. Weidemann 2, Matt Gleeson 2, A. Gooden, M. Clarke.
Best: HOLBROOK: M. Duryea, T. Aylmore, M. Shaw, Jarrod Hillary, N. Coutts, Josh Hillary, D. Hargreaves, T. Nichols; OSBORNE: A. Gooden, D. Flanigan, D. Howard, O. Gooden, J. Grieve, T. Geddes, H. Gleeson.
